1: 81 percent / LiAlH(OtBu)3 / tetrahydrofuran / -10 °C 2: 81 percent / 4-pyrrolidinopyridine / CH2Cl2 3: 89 percent / lithium hydroxide / H2O; tetrahydrofuran / 0 °C 4: 88 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 5: 66 percent / 2,6-lutidine / CH2Cl2 / -20 °C 6: 88 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 0 - 20 °C 7: 81 percent / potassium carbonate / dimethylformamide / 20 °C 8: 78 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 - -20 °C 9: 80 percent / dimedone / [Pd(PPh3)4] / tetrahydrofuran / 20 °C 10: PhI(OAc)2 / acetonitrile; H2O / 0 °C 11: 2,9-dimethyl-1,10-phenanthroline; pyridine / CH2Cl2 / 20 °C 12: 61 percent / pyridine*HF / tetrahydrofuran / 50 °C View Scheme